Regiospecific N-alkyl substitution tunes the molecular packing of high-performance non-fullerene acceptors

Qi, Feng; Jones, Leighton O.; Jiang, Kui; Jang, Sei-Hum; Kaminsky, Werner; Oh, Jiyeon; Zhang, Hongna; Cai, Zongwei; Yang, Changduk; Kohlstedt, Kevin L.; Schatz, George C.; Lin, Francis R.; Marks, Tobin J.; Jen, Alex K.-Y.

doi:10.1039/d1mh01127h

Regiospecific N-alkyl substitution tunes the molecular packing of high-performance non-fullerene acceptors

Journal Article · Fri Oct 01 00:00:00 EDT 2021 · Materials Horizons

DOI:https://doi.org/10.1039/d1mh01127h· OSTI ID:1978803

Qi, Feng ^[1]; ^[2]; ^[3]; Jang, Sei-Hum ^[4]; Kaminsky, Werner ^[4]; Oh, Jiyeon ^[5]; Zhang, Hongna ^[6]; ^[7]; ^[5]; ^[2]; Schatz, George C. ^[2]; ^[3]; ^[2]; Jen, Alex K.-Y. ^[8]

City University of Hong Kong, Kowloon (Hong Kong); OSTI
Northwestern University, Evanston, IL (United States)
City University of Hong Kong, Kowloon (Hong Kong)
University of Washington, Seattle, WA (United States)
Ulsan National Institute of Science and Technology (UNIST) (South Korea)
Hong Kong Baptist University, Kowloon (Hong Kong)
State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Kowloon, 999077, Hong Kong
City University of Hong Kong, Kowloon (Hong Kong); University of Washington, Seattle, WA (United States)

The rapid development of non-fullerene acceptors (NFAs) with strong near-infrared absorption has led to remarkably enhanced short-circuit current density (J_sc) values in organic solar cells (OSCs). NFAs based on the benzotriazole (Bz) fused-ring π-core have great potential in delivering both high J_sc and decent open-circuit voltage values due to their strong intramolecular charge transfer with reasonably low energy loss. Here in this work, we have designed and synthesized a series of Bz-based NFAs, PN6SBO-4F, AN6SBO-4F and EHN6SEH-4F, via regiospecific N-alkyl engineering based on the high-performance NFA mBzS-4F that was reported previously. The molecular packing of mBzS-4F, AN6SBO-4F, and EHN6SEH-4F single crystals was analyzed using X-ray crystallography in order to provide a comprehensive understanding of the correlation between the molecular structure, the charge-transporting properties, and the solar cell performance. Compared with the typical honeycomb single-crystal structure of Y6 derivatives, these NFAs exhibit distinctly different molecular packing patterns. The strong interactions of terminal indanone groups in mBzS-4F and the J-aggregate-like packing in EHN6SEH-4F lead to the formation of ordered 3D networks in single-crystals with channels for efficient charge transport. Consequently, OSCs based on mBzS-4F and EHN6SEH-4F show efficient photon-to-current conversions, achieving the highest power conversion efficiency of 17.48% with a Jsc of 28.83 mA cm^-2.

View Accepted Manuscript (DOE)

Research Organization:: Northwestern University, Evanston, IL (United States)

Sponsoring Organization:: City University of Hong Kong; Guangdong-Hong Kong-Macao Joint Laboratory; Office of Naval Research (ONR); Research Grants Council of Hong Kong; USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001059

OSTI ID:: 1978803

Alternate ID(s):: OSTI ID: 1826620

Journal Information:: Materials Horizons, Journal Name: Materials Horizons Journal Issue: 1 Vol. 9; ISSN 2051-6347

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Regiospecific N-alkyl substitution tunes the molecular packing of high-performance non-fullerene acceptors

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